$45,000,000
8 Beds ⋅ 8 Baths ⋅ 409860 MLS ⋅ Fee Simple Tenure
An exceptionally rare opportunity to acquire two side-by-side oceanfront properties that creates a private coastal compound in one of South Maui’s most coveted enclaves. Positioned approximately 40 feet above a pristine crescent-shaped white sand beach this offering delivers a setting that cannot be duplicated under current coastal regulations. Behind a gated entry, the combined estate offers unmatched scale, privacy, and flexibility ideal as a legacy family retreat, multi-generational compound, or secure oceanfront enclave. Expansive decks from 2 distinct residences project toward the horizon, capturing sweeping panoramic views from Makena to the West Maui Mountains, with year-round sunsets and an ever-changing Pacific backdrop. A gated footpath leads to a secluded stretch of sand known as “Secret Beach,” offering rare, near-private access just steps from your door. Opportunities of this magnitude—two contiguous oceanfront parcels with elevation, privacy, and direct beach access—are extraordinarily limited. Offered together, this is a chance to secure a one-of-one compound in a supply-constrained market where replacement is simply not possible. Minutes from Wailea’s world-class golf, dining, and shopping, yet worlds apart in privacy and setting. Legacy property. Irreplaceable location. Finite opportunity. **Disclosure, some images have been virtually staged**

4640 & 4650 Makena Rd, Kihei

Listing courtesy of Hawaii Life (W).

$37,000,000
408242 MLS ⋅ Fee Simple Tenure
MAKENA RANCH -160 ACRES OF OCEANVIEW LEGACY LAND Offered at $37 Million I Fee Simple Makena Ranch encompasses approximately 160 acres across 13 agricultural-zoned parcels along Maui's prestigious Makena Road-one of the largest privately held tracts on the island's southern coast. This gated ranch features private access, a paved internal driveway, underground electrical service, and a redundant, large-capacity private water system supporting both domestic and fire-protection needs. Designed with flexibility in mind, the property offers off-grid or hybrid power potential through private power generation systems. Sweeping ocean, mountain, and neighbor-island views span from La Perouse Bay to Big Beach, showcasing Maui's most dramatic coastline. Multiple building sites across the parcels provide exceptional options for a private estate compound, multi-residence development, or agricultural retreat. Combining scale, seclusion, and readiness, Makena Ranch represents an unparalleled opportunity to own a secure, fee-simple legacy asset in one of Hawaii's most exclusive regions. Listor has a financial interest in the property.

7191 Makena Rd, Kihei

Listing courtesy of Coldwell Banker Island Prop-Ku.

$26,500,000
6 Beds ⋅ 6 Baths ⋅ 409734 MLS ⋅ Fee Simple Tenure
THE ULTIMATE MAUI DREAM . .The most sophisticated are no longer asking where to live . .They are asking, “Where can we breathe?” Welcome to The Makena Generational Oceanside Retreat offering resort-style living with smart-home technology, unobstructed ocean & sunset views, Haleakala sunrise views situated on a professionally landscaped one-acre gated and walled tropical estate.The fully operational compound is ready for occupancy offering a vast combination of energy efficiency, self-sufficiency and refined comfort featuring the largest residential Tesla Solar Roof in the US installed in 2024. A unique opportunity to own a private Maui sanctuary of this stature where luxury, wellness and sustainability coexist in harmony. The indoor-outdoor lifestyle is designed for multigenerational living, executive retreats and legacy ownership. In a world moving faster than ever, it is intentionally crafted for life to slow down. Extensively upgraded under the current owner with substantial infrastructure, aesthetic and technology enhancements, the property is now offered well below current replacement cost. The Makena community remains one of Maui’s most coveted luxury destinations. The current property manager creates effortless luxury living with lock-and-leave convenience. The luxurious amenities are endless. The privately separated interior living areas offer exceptional craftsmanship, premium wood finishes, floor-to-ceiling bifold glass doors, elevator, gourmet kitchen, exercise area, massage room, sauna, and steam shower. The dramatic custom water features include a puka lava entry waterfall with pond and interior floor-to-ceiling water feature at the base of the floating staircase. The additional luxury oceanside pool home with its oversized heated pool includes its own gourmet kitchen, Italian brick pizza oven and rear projection entertainment system. Combined with many additional features, the estate offers a total of 8b-8b comfortably accommodating up to 16 guests. Parking is a breeze with a 4+car garage and generous additional parking areas.

7505 Makena Rd, Kihei

Listing courtesy of Compass-W.

$26,000,000
3 Beds ⋅ 5 Baths ⋅ 410474 MLS ⋅ Fee Simple Tenure
What can money buy that time can't? Six years of thoughtful planning, design, construction, and mature landscaping, ready today. Spanning 4.35 acres across two adjoining parcels, including a rare buildable two-acre lot, 215 & 217 Plantation Club Dr. is a wellness retreat for those who value privacy, health, and the freedom to disconnect. Perched 325 feet above sea level in a lush West Maui microclimate and sited according to Chinese feng shui principles, the estate captures panoramic views of Moloka'i, Lana'i, and the Au'au Channel, where humpback whales winter and calve. Across the road is Honolua Bay, Maui's iconic surf break, with the Plantation Golf Course 200 yards away. Recovery is built into the architecture. The primary suite features a 15-foot rain shower and soaking tub, while the pool house includes a Pilates studio and aromatherapy steam shower. Outside, a heated 22-by-60-foot saltwater pool, spa, and cold plunge create a daily ritual of restoration. This isn't a house with amenities. It's a private wellness compound with bedrooms attached. More than 90 fruit trees across 16-plus varieties are irrigated by a private cistern, complemented by an outdoor kitchen with a wood-fired pizza oven. A detached five-car garage with high-lift doors accommodates 10 vehicles. Fully furnished in Plantation Estates near Kapalua Resort, beaches, golf, and dining. Offered below replacement cost - an opportunity that can't be recreated today.

215 Plantation Club Dr, Lahaina

Listing courtesy of Compass-W.

$24,500,000
4 Beds ⋅ 6 Baths ⋅ 408751 MLS ⋅ Fee Simple Tenure
One-of-a-Kind Keawakapu Beachfront Estate in one of Maui’s most coveted oceanfront settings, offering an extraordinary blend of irreplaceable beach proximity, modern structural integrity, and timeless refined island design. The residence was completely rebuilt from the foundation up, completed in 2013—retaining only the original pool and foundation to preserve its rare, grandfathered beachfront setback. The result is a fully reimagined wood-framed home enhanced with structural steel beams, allowing for expansive open spans and a modern layout. The estate includes a spacious main residence, separate guest home, and three-car garage, creating a private compound ideal for multigenerational living or luxury hosting. Designed for unforgettable gatherings, multiple indoor and outdoor living spaces flow effortlessly to a spectacular resort-style pool with slide, hot tub, waterfalls, and dramatic rock grotto. A distinctive basement level serves as the ultimate retreat, featuring a game room with custom Koa wood bar, in-home gym, craft room, and additional guest suite with full bath. Lush tropical landscaping, sauna, and multiple outdoor showers enhance the resort-caliber experience. The chef’s kitchen and dining area showcases Sepalle wood detailing and striking Labradorite granite countertops, blending warmth with sophistication. The primary suite is a sanctuary, complete with a spa-inspired bath featuring a floating tub, private sundeck, and panoramic Haleakala views. Throughout the property, incredible details and textures create a custom, curated feel. Meticulously rebuilt in 2013 to combine modern structural capability with an irreplaceable oceanfront location, this legacy beachfront estate represents a rare and irreplaceable offering on Maui.

3060 S Kihei Rd, Kihei

Listing courtesy of Coldwell Banker Island Prop(S).

$24,500,000
5 Beds ⋅ 6 Baths ⋅ 408059 MLS ⋅ Fee Simple Tenure
Experience the pinnacle of oceanfront luxury in this stunning, 5 bedroom, 5 bath, plus 2 half bath, 7,244 sq. ft. home estate. This over a half-acre property is located within the ideal stretch of Keawakapu Beach, offering unparalleled access to Maui’s most coveted shoreline. This architectural triumph blends contemporary elegance and convenience with the island’s natural beauty, creating a private sanctuary of sophistication and rare serenity. This estate features 5 spacious en-suite bedrooms, multiple areas for relaxed socializing, and a seamless indoor-outdoor flow that embraces the home’s stunning pool courtyard and oceanfront experience. Every room gifts an extraordinary vantage point of paradise – between sweeping ocean views in three master suites or tranquil poolside perspectives from the guest suites. At the heart of the home, the expansive pool and courtyard form a striking focal point, linking the media room, main entry, and living areas in perfect harmony. A private poolside retreat ensures both security and discretion, ideal for intimate gatherings or large-scale entertaining. Landscaped gardens with numerous palm trees and second-level sundecks off the guest suites provide elevated spaces to soak in a front seat view of unforgettable sunsets. A spacious oceanfront lawn offers ultra-privacy, featuring a fire pit that creates an inviting ambiance, shielded from public view and accessible only through a discreet, gated beach entrance. Whether you seek a primary residence, a lavish vacation home, or an island retreat, this estate is designed for those who desire premium beachfront living with an ultimate feel of privacy. A rare opportunity to own the most memorable oceanfront lifestyle in Maui.

3254 S Kihei Rd, Kihei

Listing courtesy of Hawaii Life (W).

$23,000,000
4 Beds ⋅ 5 Baths ⋅ 402062 MLS ⋅ Fee Simple Tenure
Nestled along the prestigious Makena coastline, 7595 Makena Road represents the pinnacle of contemporary Hawaiian luxury living. This extraordinary residence stands as a masterpiece where architectural innovation meets paradise. Perched on an expansive and private one-acre lot, this four-bedroom haven commands breathtaking views of the mesmerizing Ahihi Bay, where emerald and turquoise waters dance in eternal harmony. Each morning brings nature's theater to your doorstep, with the gentle lapping of waves providing the perfect soundtrack to your day. The dwelling is comprised of a total of 6643sf: 4778sf of living space, 995sf of covered lanai space to enhance the indoor/outdoor living, and an oversize, three-car garage of 870sf. The home's thoughtful design seamlessly integrates indoor and outdoor living spaces, featuring: - Four luxurious en-suite bedrooms, each offering a private sanctuary - Open-concept baths with spacious showers and captivating ocean views - State-of-the-art smart home technology throughout - Private elevator ensuring effortless accessibility - Custom finishes that reflect both modern luxury and island charm As one of Makena's newest luxury estates, this residence offers more than just a home – it's an invitation to experience Maui's most coveted lifestyle. The property's privileged location provides the perfect vantage point for witnessing the island's legendary sunsets and seasonal whale watching. Built in 2022, this contemporary masterpiece represents the perfect blend of modern amenities and timeless island elegance. Every detail has been carefully curated to create an environment where luxury isn't just a feature – it's a way of life. This rare offering stands as a testament to sophisticated island living, where every detail has been thoughtfully designed to create an unparalleled living experience in one of Maui's most sought-after locations. Don't let this unparalleled Makena estate slip away – seize the opportunity to be the first owner of this exceptional estate.

7595 Makena Rd, Kihei

Listing courtesy of Compass-W.

$19,750,000
4 Beds ⋅ 5 Baths ⋅ 407563 MLS ⋅ Fee Simple Tenure
Basking in the breathtaking beauty of Maui, perched just 25 feet from the shoreline, 51 Hui Road E is more than an oceanfront estate – it is a living work of art. Built entirely in reinforced concrete and completed with precise craftsmanship, this timeless villa is as enduring as the island itself. Each pillar sinks deep into the volcanic foundation, giving this island masterpiece a quiet strength that mirrors the steady rhythm of the Pacific. Its proximity to the ocean can never be duplicated. The exotic architecture fuses Mediterranean grace with tropical ease. It celebrates both endurance and grace. It is a home designed, not merely to exist beside the ocean, but to belong to it – to draw strength from its power and beauty from its calm. Its most recognizable feature, a glowing orange palapa overlooking the ocean is perfect for casual outdoor living and dining. It offers surreal views of shimmering sunsets that stretch to the jewels of Lanai and Molokai as well as a serene vantage for watching whales in season. Steps away, the heated pool finished in mosaic tile mirroring the sea and an inset spa await. Garden pools, a koi pond, and lush, mature landscaping enhance the setting. Inside, the villa unfolds in layers of artistry and intimacy. The grand salon with its 17-foot vaulted ceilings, arched colonnades, Italian fountain, and romantic star shaped skylights set a tone of cultivated elegance. The chef’s kitchen discretely tucked away, honors traditional European service design – a private culinary domain outfitted with professional appliances, handcrafted cabinetry, and artisanal tile work. The primary suite is an ode to serenity. A four-poster bed faces an arched lanai framed in tropical vines opening to the sea beyond. Morning light spills across white stone floors while a hand-tiled fireplace and soft coastal hues evoke both romance and repose. In the adjoining bath, marble, crystal, and natural light converge. A soaking tub is framed by palms and ocean views. The library reveals the home’s most personal voice: coral-colored walls, a hand-painted ceiling, and imported carved wooden doors that open into a space of warmth. A place where art, books, and tropical light are in quiet harmony. A second wing includes guest accommodations, a magnificent wine storage area, and laundry facilities. Gates to the property open to a large motor court and garage with ocean views as well as custom work bench and additional storage. The immense substructure offers additional flexibility, not included in the living area square footage. Minutes from Kapalua Resort, yet entirely private, 51 Hui Road E stands as one of Maui’s most extraordinary oceanfront estates – where art, engineering, and the eternal rhythm of the Pacific meet in perfect harmony.

51 Hui Road E, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$19,750,000
7 Beds ⋅ 9 Baths ⋅ 406991 MLS ⋅ Fee Simple Tenure
This magnificent oceanfront West Maui estate rests on approximately 1/2 acre of prime land in Kahana with over 250 feet of ocean frontage. Perfectly located between Kaanapali and Kapalua Resorts, this oceanfront property has no equal in the Hawaiian Islands. This nearly 10,000 square foot residence epitomizes Pacific Rim architecture. Glass pocket doors slide into rock walls bordering the spacious great room, which includes a grand living and dining area, as well as a fabulous open kitchen with separate enclosed butler's pantry. A floating mezzanine soars above the great room with a phenomenal sports bar and game tables. There are seven oceanfront suites, one being utilized as a media suite and one as a gym, each with a luxurious bath and most with a wet bar. Every suite is oceanfront with sweeping views of the neighboring island of Lanai and glimpses of Molokai. The large primary suite offers complete privacy and a fabulous outdoor lanai. The primary bathroom features an Italian custom two-person stone Jacuzzi tub, exquisite stonework, built-in wall speakers, and an expansive closet. An attached oceanfront one-bedroom Ohana can be utilized as a private office, for guests, or a caretaker. Extensive enhancements to the property include a new roof with 60KW photovoltaic solar system. Throughout the interior a selection of doors were replaced with new 10 ft. doors, freshly stained wood, new screens, and high-efficiency shades. A new Hydraulic elevator was installed, as well as new commercial-grade high efficiency air conditioning systems. Electronics have been significantly improved with a Control 4 System, a new Lutron system, top-of-the-line speakers throughout, as well as a state-of-the-art security camera system. A custom pool, complete with spa and waterfalls, is easily accessible from the great room. Moving outdoors, the oceanfront lanai and grilling area offer expansive coastal views. An outdoor landscape sound system has been integrated into the tropical gardens along with Tiki gas lamps and a fire pit from a local artist. The driveway was redesigned for convenience with the addition of a second entrance. Custom wood gates give the vehicular and pedestrian entrances a sophisticated natural appeal. Offered turnkey.

4809 Lower Honoapiilani Rd, Lahaina

Listing courtesy of Coldwell Banker Island Prop-KP.

$16,950,000
5 Beds ⋅ 6 Baths ⋅ 410130 MLS ⋅ Fee Simple Tenure
Perched on Maui’s coveted west side, this extraordinary 8-bedroom private estate offers a level of luxury, privacy, and craftsmanship rarely seen in Hawai'i. More than a home, this is a legacy estate, an irreplaceable Maui sanctuary designed for those who accept nothing less than extraordinary. Located in the coveted Plantation Estates at Kapalua community on the incredible 16th hole of the world-class Plantation Course, the property commands unmatched sweeping panoramic views across the Pailolo Channel framed by the stunning views of the outer islands of Lana'i and Moloka'i. Designed without compromise, the 2-acre estate encompasses more than 8,200 square feet across two separate residences, creating a private retreat unlike any other. Resort-caliber amenities include an infinity-edge pool and dual spas, private office, theater and fitness center. The 7,200 square foot 5-bedroom 5.5 bath main residence seamlessly blends indoor and outdoor living through expansive custom pocket sliding doors that open to reveal breathtaking ocean vistas and unforgettable sunsets. Rich natural materials, custom African Mahogany millwork, exotic stone, and world-class finishes define every space, from the chef’s kitchen and grand great room to the spectacular primary suite. A fully appointed three-bedroom guest cottage with its own pool, fire-pit and Palapa set over a koi pond provides exceptional accommodations for family, guests, or staff while maintaining complete privacy. Aside from world-class golf, the Kapalua resort offer the utmost in amenities including award-winning spa, tennis and pickleball, exquisite dining options and some of the finest beaches: Fleming Beach, Oneloa Bay and Kapalua Bay, which was rated as the Best Beach in America by Conde Nast Travel Magazine.

706 Mokuleia Pl Unit 6, Lahaina

Listing courtesy of Keller Williams Realty Maui-L.

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